Piperidine → 3-(6-Morpholin-4-yl-pyridin-3-yl)-acrylic acid methyl ester

HRID 2265939Notes

Reaction equation

HRID 2265939 reaction equation
[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9](Br)=[CH:10][CH:11]=1.[NH:14]1[CH2:19][CH2:18]C[CH2:16][CH2:15]1.CC[O:22]C(C)=O>>[CH3:1][O:2][C:3](=[O:13])[CH:4]=[CH:5][C:6]1[CH:7]=[N:8][C:9]([N:14]2[CH2:19][CH2:18][O:22][CH2:16][CH2:15]2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 8082PiperidineHCID 8857Ethyl AcetateHCID 714275823-(6-Bromopyridin-3-yl)acrylic acid methyl ester

Product 1

HCID 687853973-(6-Morpholin-4-yl-pyridin-3-yl)-acrylic acid methyl esterYield 21%

Procedure

3-(6-Bromo-pyridin-3-yl)-acrylic acid methyl ester (100 mg, 0.413 mmol) was added to piperidine (1 ml) and the mixture was stirred for 1.5 hrs at room temperature. The reaction mixture was diluted with EtOAc and then washed three times with H2O, brine, dried. Na2SO4, filtered and concentrated under reduced pressure. The obtained residue was column-chromatographed to yield 3-(6-Morpholin-4-yl-pyridin-3-yl)-acrylic acid methyl ester (40 mg, 21%).

Workup

  1. washwashed three times with H2O, brine
  2. customdried
  3. filtrationNa2SO4, filtered
  4. concentrationconcentrated under reduced pressure
  5. customThe obtained residue was column-chromatographed

Sources & evidence

ORD record
ord-b194ff5c54cf4669b917b6e0d033b93d
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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